


Pickpocket

by destieldrabblesdaily



Category: Supernatural
Genre: AU, M/M, Strangers to Lovers
Language: English
Status: Completed
Published: 2015-12-15
Updated: 2015-12-15
Packaged: 2018-05-06 22:58:14
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,532
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/5433989
Author URL: https://archiveofourown.org/users/destieldrabblesdaily/pseuds/destieldrabblesdaily
Summary: <blockquote class="userstuff">
              <p>Written for this prompt: 'Dean needs money for food for him and Sam (John leaves them alone at a motel again) so he picks pockets, but a handsome rich young man who is his age (Cas), catches Dean picking his pocket and ends up buying groceries for the brothers, then takes Dean out on a date.'</p>
            </blockquote>





	Pickpocket

Five days until Christmas eve. While looking for a new victim, Dean rubbed his hands together in a futile attempt to warm them up. His fingers were numb, but he reminded himself that he had bigger problems to worry about.

 _Sammy. Money to buy food for Sammy._  That was the one thought keeping him from feeling guilty about his less than noble plan.

Needless to say, he’d felt guilty about it the first time. And the second time, maybe even the third. But he had no other choice, dammit. Being stuck in a motel room with dad gone on one of his crazy quests for the rest of the week, leaving behind barely enough food for one person to eat… Dean saw no other options. There was no point in looking for a job; no one would bother to hire a seventeen year old without experience who’d be gone by the end of the week. Which meant that it was either this, or starving.

The main street of whatever town they were currently staying in -Dean had given up on keeping track- was crowded, people rushing left and right, here for their last minute Christmas shopping. Caught in a sea of twinkling Christmas lights, Dean scanned the stores on his left, colorful Christmas decorations greeting him from behind display windows.

He stumbled on his feet when a middle-aged lady abruptly bumped into him, taking him by surprise. She muttered an apology, looking extremely stressed-out as she continued on her way, carrying at least ten extra-large shopping bags. Yeah, celebrating Christmas seemed like a whole bunch of fun.

Dean rolled his eyes at her before turning to observe the stores at the other end of the street. He noticed that several people were window shopping there.  _Perfect._  Some of them were obviously busy drooling over all the crap that they couldn’t afford anyway; too preoccupied to watch their pockets and purses.

There was a young couple, both of them looking wistfully at the giant flat screen televisions behind the glass. They weren’t carrying any shopping bags, an indicator that they didn’t have much to spend. Not the best choice then. Dean moved on, and a young man with dark hair caught his eye.

He was wearing a black trench coat, a midnight-blue scarf, and shiny black dress shoes. The guy appeared to be waiting for someone, just standing there, thumbs fumbling with an expensive looking phone, eyes locked on the screen. He couldn’t be much older than Dean, but he looked wealthy for sure. The bonus? He was too engrossed in whatever he was doing on his phone to ever notice someone picking his pocket. Definitely worth a shot.

“Here it goes…” Dean mumbled to encourage himself, taking one last deep breath before pushing through the crowd, eyes never straying from his target.

Closer _, closer_. He slipped past the couple that he’d spotted earlier, seeing that the dark haired guy was still staring down at his phone. This was going to be a piece of cake. Two more steps and Dean was close enough. Close enough to reach out and-

“Hey!” A deep voice warned, long fingers securing themselves around Dean’s wrist just as he was about to explore the left pocket of the guy’s fancy coat.

“Shit.” Dean cursed, mortified, gazing right at the guy holding him in a firm grip, realizing that they were the exact same height as they were standing there nose to nose.

Blue eyes were curiously assessing him, and holy crap, from up close Dean quickly concluded that this guy had to be the winner of a genetic jackpot of some sort. Rich  _and_ gorgeous. Not fair.  

Admittedly, Dean knew that he could appreciate the occasional dude, but this was a whole different matter. Prominent cheekbones, soft pink lips, chiseled jaw, artfully tousled hair… Dean’s brain went offline as he ogled the stranger that he’d been trying to rob less than a minute ago.

“I’ll go ahead and say that there’s no need for me to ask what you were trying to do.” The guy stated calmly, hardly looking offended as he called Dean out on his crimes.

“I ehm-” Dean stuttered, feeling a lump form in his throat.

“You?” The stranger prompted patiently, still not letting go of Dean’s wrist.

And then Dean started rambling. He couldn’t tell what it was; probably the eyes, he wouldn’t be shocked in the least if those pools of blue held hypnotic powers.

“Look man, I’m sorry, alright? I didn’t mean to, I mean I  _did_  mean to, but all I want to do is buy some food for my little brother. A twelve year old kid deserves better than always surviving on a handful of Lucky Charms… Especially around Christmas.”

To Dean’s surprise, those icy blue eyes immediately turned softer, the look in them almost contemplative.

“What is your name?” The stranger inquired, his face not giving away much.

“Dean… Dean Winchester.” Dean answered truthfully in a whisper, despite his dad having taught him to always use a false name, no exceptions.

“Dean Winchester.” The guy nodded slowly as he repeated Dean’s full name. “It’s a pleasure meeting you, I’m Castiel Novak… Now, you’re going to tell me where you’re staying, and then I’m going to make a phone call.”

Dean’s stomach turned as the guy, Castiel, finally loosened his hold on Dean’s arm.  _Awesome._  He was going to spend Christmas in jail, wasn’t he? His dad was going to go berserk. Fan-freaking-tastic.

Knowing that it was a lost cause anyway since he’d already given the guy his full name earlier, Dean gave the address of the motel where he was staying, helplessly waiting when Castiel turned away to make his phone call in a hushed tone.

Full of nerves, Dean didn’t know what to think when Castiel hung up and turned his attention back to Dean, smiling warmly.

“You’re free to go now.” He said before Dean even dared to ask. “But we’ll see each other again.  _Soon_.”

After briefly letting his hand linger on Dean’s shoulder, Castiel turned away with one last tiny smile. Dean stared after him as he disappeared in the crowd, too stunned to go after the guy.

He sighed, shoulders slumped, not feeling too great about everything that had happened just now. There were going to be some nasty-ass consequences, that was a given.

~

After dejectedly wandering the streets some more and scoring another box of Lucky Charms thanks to the last money that he had left, Dean eventually made his way back to the motel, his toes all but freezing off.

The last thing he’d expected when opening the door to their smelly room, was the sight of a very excited Sam, practically bouncing up and down.

“Dean! You will not believe this!” He exclaimed, eyes wide as he pointed to the small table in the corner. “This really nice lady named Anna was here, you just missed her! She said that your friend Castiel is her brother, and she brought candy! So much candy! And a lot of healthy food too, I guess… But  _candy_ , Dean!”

Dean stilled, brow furrowed as his eyes fell on the countless bags on the floor, all of them stuffed with groceries.

Well,  _shit_. Clearly, Castiel was not only attractive, but also generous. Dean felt his heart grow in his chest, knowing what this random stranger had done for him.

“What are we having for dinner, Dean?” Sam asked, tugging at Dean’s sleeve, pulling him out of his daze.

Dean grinned down at his little brother, ruffling his hair, which earned him a displeased groan from Sam.

“We’ll have whatever you want, Sammy. Whatever you want…”

~

_Knock knock._

There was a tap at their door just as Dean was about to pick something for tonight’s dinner, memories of last night’s unexpected feast still on his mind.

“I’ll get it!” Sam called, getting up from the bed and abandoning the TV.

Dean didn’t stop him, but his heart thumped against his ribcage when he heard the deep gravelly voice that he easily recognized.  _Castiel._

“It’s for you.” Sam announced, knowingly wiggling his eyebrows at Dean before flopping down on the bed again, grabbing the remote to flick through channels.

Hesitant, Dean shuffled to the door, coming face to face with his savior. He could feel his face turn red, because  _crap_ , the guy was as handsome as Dean remembered him being after their awkward encounter yesterday.

“Hello, Dean.” Castiel greeted him pleasantly.

“Heya, Cas… tiel.” Dean responded, smiling timidly. “Really dude, thanks for the-”

Castiel held up a hand to silence him. “It was my pleasure, but that’s not what I’m here for… I’m here because I was wondering if you had any plans for tonight?”

Dean gaped at the guy, completely tongue tied. In the background, Sam was making kissing noises. Dean was going to slap his little brother. Gently.

~

Closing his eyes, Dean moaned as he tasted the best steak that he’d ever had in his life. From across the table, Castiel chuckled, his eyes examining Dean with care.

“You seem to approve of the restaurant that I chose for us tonight, I’m glad.”

“Hell yeah, who wouldn’t approve of this!” Dean praised, beaming back at Castiel.

The atmosphere was light, and Dean felt better than he had in a long time, if not ever. Anna had offered to look after Sam for the night, and so for once, Dean didn’t have a single care in the world.

Surprisingly, Cas was easy to talk to, even if they were from entirely different worlds.

Castiel’s family, as it turned out, owned a billion dollar company, and his parents were never opposed to Cas using their money for causes that they deemed worthy, such a feeding people less lucky than them. Castiel himself was in college, but currently home for a Christmas break. He’d turn twenty next month, and it made Dean wonder how someone that young and privileged could already be that kind and considerate towards total strangers.

Dean ended up giving a lot of his secrets away that night as well; about his dad, and this crazy quest of his to find his wife’s murderer. About how it had affected their lives for years, their dad looking for help by going to the wrong kind of people and traveling from town to town, obsessed with his revenge.

When the night ended and Castiel walked Dean back to the motel, Dean was genuinely disappointed that their time was up.

They paused when they reached the parking lot, for a moment just staring at each other, but Dean blinked when he saw how fragile flakes of snow began to fall all around them.

“White Christmas, huh?” He joked to break the tension.

Castiel laughed quietly. “Who would’ve thought?”

Another prolonged stare, and then, without warning, Castiel’s strong hand carefully cradled Dean’s cheek. Dean leaned into the warmth, somehow unafraid to let his feelings show in front of Castiel.

“I like you, Dean Winchester.” Castiel bluntly declared without shame, making Dean’s heart do somersaults. “You’re a good brother, you have a big heart, and you’re very bright. But I want you to think about what you want in life,  _for you_. Proper education, going to college… And when you figure it out, I need you to let me know, so that I can help you, at least financially.”

Tears were burning in the corners of Dean’s eyes, overwhelmed by this much kindness and support, something he hadn’t known ever since his mother had passed away. Not that he could ever accept Castiel’s offer, that was  _insane_.

“It’s too much, Cas.” He argued, voice breaking. “Even if that’s what I wanted, it’s too much. Besides… I can’t leave Sammy behind.”

Castiel shook his head, seeming almost amused. “You are unbelievable. You think I’d help you, but not your brother, the one you care about most? He would be part of the deal, I’d make sure to take care of him as well, I swear it.”

Dean chewed his lower lip, unable to take his eyes off of Castiel, Cas’ thumb now soothingly stroking his jaw.

“Just let me know when you’re ready, Dean… What do you want?”

All of Castiel’s words robbed Dean of his own vocabulary.  _What did he want?_ At seventeen, that was a tough question, even for teenagers who were living a life a lot less complicated than Dean’s.

“I want…” He didn’t finish that sentence, giving up, instead leaning in until his lips were an inch away from Castiel’s.

To Dean’s relief, Cas took the hint, and not much later lips were touching, Castiel holding Dean close, strong hands resting on Dean’s hips, grounding him. It was the kind of kiss that Dean wished could last forever, but he knew that nothing was infinite.

When they parted, Castiel rested his forehead against Dean’s temple as he tried to catch his breath.

“Think about it. Even if you want a better future for you and your brother but nothing more of this, of  _us_ , I’d still help you. You could even pay me back later if it would make you feel better.” He murmured into Dean’s ear, making Dean shiver.  _“Just let me know.”_

_~_

The day before they were leaving town, a package was delivered to their motel room. Sam gasped in awe upon discovering what was inside; a brand new cellphone.

Dean on the other hand, was more impressed by the handwritten note that came with it.

_‘The bill has been taken care of for the next six months, I would like to keep in touch with you and text you._

_PS: Always remember that you promised to let me know when you figure it out._

_Castiel’_

For the first time in seventeen years, Dean caught himself believing that good things do happen.

~

**_Six years later_ **

Dean liked being the little spoon, that much he’d learned about himself over the past five years.

“Good morning, Dean.”

No matter how many times those words had been whispered against the nape of Dean’s neck, they would never get old.

“Morning, Cas.” He breathed, smiling at the sunlight that streamed in, caressing his face.

Castiel’s arms tightened around his waist as he whispered “Congratulations, again.”

Dean huffed. “Graduation was two days ago, Cas. Can we let it go already?”

Castiel laughed; Dean’s grumpiness was something that he found eternally entertaining. “I’m simply proud because my fiancé is a genius, don’t ruin it for me.” He teased.

“You’re hilarious.” Dean grumbled sarcastically, elbowing Cas in the ribs. “When summer break ends, you can direct your enthusiasm at Sammy and cheer for him instead.”

“You know I will. He’s going to make a magnificent lawyer.” Castiel shot back without missing a beat, kissing the top of Dean’s head.

They indulged in the bliss of Sunday morning silence for a good ten minutes, both reveling in the comfort of their embrace. It was Dean who spoke first when a thought came to him.

“Hey Cas?”

“Yes, Dean?”

“I’m glad I tried to pick your pocket.” Dean confessed dryly.

He felt how Castiel smiled into his hair.

“Me too, Dean…  _Me too.”_

**Author's Note:**

> For more Destiel stories, go to destieldrabblesdaily.tumblr.com


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